Finding the right bike(s) for me was also a learning process that took a few years and a few bikes.
I started out with a steel Giant Rincon rigid mtn bike. I didn't know anything about bikes, but it took me all over town and lots of commuting, shopping and yard saling(!)
Then I met my bf. He knows a lot about bikes. I learned a bit and decided I was ready to move up a bit. I decided I wanted a touring type bike and got a Novara Safari (mtn type touring bike) on sale for about $400. I rode that for a couple of years, mostly as a commuter, and then wanted something a bit faster. So I got a Trek 520 touring bike. I rode that bike for a few years, as a road and touring bike. When I decided I wanted a road bike, I had a much better idea of what I wanted. Using the measurements off the Trek 520 my bf helped me choose a Surly Pacer frame and a group that would suit my needs. I have been riding the Pacer for 4 years and I love it.
The Giant Rincon was sold to some friends of ours and it still gets ridden quite a bit.
I came across a NOS Novara Randonee frame (steel) for $15! So I replaced the aluminum Novara Safari frame with that, (I prefer steel) and sold off the Safari frame. The Randonee is my commuter now.
I got a Haro V4 hard tail mtn bike when bf was working for a Haro dealer. It was my first mtn bike with a shock. I don't mtn bike much, so I didn't want an expensive bike. Then I got a steel Gunnar Rockhound hard tail frame on ebay and moved the parts off the aluminum V4 and sold the frame.
I liked my first Surly so much that I wanted another. I wanted a Long Haul Trucker touring frame. I felt my 520 was a bit long in the top tube, the LHT is 2 cm shorter. So I got the LHT and sold off the 520 frame.
I can say I'm presently quite satisfied with all my bikes right now, not looking to buy another one or change much of anything on any of them. Never mind that I have ridden very little in the past couple of months, due to a Calculus class taking over my life! (The bikes will be there when I'm ready to ride again!)
Specialized Ruby
Gunnar Sport
Salsa Vaya Ti
Novara Randonee x2
Motobecane Fantom CXX (Surly Crosscheck)
Jamis Dragon